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WO1999026591A2 - Agent pour permanenter les cheveux ameliore - Google Patents

Agent pour permanenter les cheveux ameliore Download PDF

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Publication number
WO1999026591A2
WO1999026591A2 PCT/US1998/025169 US9825169W WO9926591A2 WO 1999026591 A2 WO1999026591 A2 WO 1999026591A2 US 9825169 W US9825169 W US 9825169W WO 9926591 A2 WO9926591 A2 WO 9926591A2
Authority
WO
WIPO (PCT)
Prior art keywords
hair
composition
phosphine
perming
tcep
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1998/025169
Other languages
English (en)
Other versions
WO1999026591A3 (fr
Inventor
John R. Lau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SDG Technology Inc
Original Assignee
SDG Technology Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SDG Technology Inc filed Critical SDG Technology Inc
Priority to AU16057/99A priority Critical patent/AU1605799A/en
Publication of WO1999026591A2 publication Critical patent/WO1999026591A2/fr
Publication of WO1999026591A3 publication Critical patent/WO1999026591A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds

Definitions

  • the present invention is directed to compositions and processes for altering the physical structure of hair. More particularly, the invention is directed to compositions and processes for perming hair.
  • the method of choice for perming hair is to use mechanical devices to form hair around tubular rollers, and use alkaline-based sulfhydryl chemical reducing agents to disrupt the hair disulfide bonds.
  • the hair is then flexible and able to set in a new configuration.
  • the disulfide bond (R1-S-S-R 2 ) in hair protein is reacted on by a chemical reducing agent containing a free sulfhydryl functional group, such as thioglycollic acid.
  • a chemical reducing agent containing a free sulfhydryl functional group such as thioglycollic acid.
  • the first product is a mixed disulfide compound containing a component of hair protein and a compound of thioglycollic acid.
  • the second product is formed as a result of the cleavage of the original disulfide bond.
  • Half of this original bond is now manifested as a free sulfhydryl compound capable of engaging in further reaction toward any disulfide linkage.
  • Thioglycollic acid is effective, but unpleasant and sometimes harmful to use. Because it functions in a harsh alkaline environment, it must be used in a careful manner to prevent eye damage and skin irritation. The odor of the perming reaction can be offensive and the time for completion of the procedure is often tiring to the recipients. Thioglycollic acid is used at an elevated pH usually between pH 9-12. During the time required for perming, the harsh alkaline environment leads to severe cuticle damage. This results in hair that is brittle and has an abrasive or rough texture. Naturally curly hair can be straightened during combing by first applying a reducing agent which reacts with the disulfide bonds.
  • the reactivity of a disulfide bond is dependent upon its polarity.
  • a molecule is considered to be polar if the center of negative charge does not coincide with the center of positive charge.
  • a molecule that exhibits this disparity in charge is called a dipole.
  • Dipoles possess dipole moments ( ⁇ ) which are equal to the magnitude of the charge, expressed in electrostatic units (e.s.u.), multiplied by the distance (d) in angstroms between the centers of charge.
  • ⁇ dipole moments
  • the overall polarity of a molecule is represented by a composite of the various polarities manifested by the individual bonds within a given molecule.
  • molecules such as H 2 , 0 2 , N 2 , Cl 2 and Br 2 , have zero dipole moments, and as a result they exhibit non-polar properties and characteristics. Since two identical atoms in each of these molecules have the same electronegativity and share electrons equally, the charge (e) is zero and therefore ( ⁇ ) is also zero.
  • H:F hydrogen fluoride
  • D Debye units
  • Molecules such as methane and carbon tetrachloride also have zero dipole moments because these molecules possess a tetrahedral structure which is symmetrical in nature. As a result of this symmetry, the partial charges are canceled. In other words, the movement of electrons toward a positive nucleus, which would create a relative electronegative center, is counterbalanced by a similar kind of movement in the opposite direction. Furthermore, molecular dipole moments can be enhanced or made larger if there is a pair of unshared electrons associated with the molecule. For example, ammonia has a dipole moment of
  • hypothesized polarity of this bond is shown as follows: phosphine and sulfhydryl nucleophiles
  • the ⁇ + end of this disulfide dipole possesses a slightly stronger affinity for the unshared pair of electrons on the incoming phosphorus or sulfur atom than does the ⁇ " sulfur atom in the disulfide bond.
  • the reaction sequence of disulfide bond breaking commences with the formation of a transition complex between the phosphine and the ⁇ + sulfur of the disulfide bond.
  • the disulfide bond assumes a polar character because it resides in a polar aqueous medium and is influenced by the electron environment of the incoming nucleophile.
  • solvent polarity can either retard or facilitate the cleavage of a disulfide bond by a reducing agent residing within a water-insoluble proteineous matrix such as hair.
  • Disulfide bonds that reside in relatively non-polar regions, such as within the centers of polypeptide helices, are not as accessible nor as readily cleaved as soluble disulfide bonds in aqueous media.
  • ionized TCEP comes in contact with positively charged amino acid residues found in hair polypeptide chains such as lysine, amino terminal glycine, histidine and arginine, ionic linkages are produced that prevent the penetration of the negatively charged TCEP molecules into the hair shaft. This effect is shown as follows:
  • O-CCH2CH2-P N-H lysine
  • TCEP has good reducing activity toward soluble disulfides in an aqueous environment and this activity can be increased by elevating the pH of the media. Since laboratory tests have demonstrated that in aqueous systems
  • TCEP has the chemical ability and adequate necleophilic activity to cleave disulfide bonds
  • the various means to enhance the penetration of TCEP through the hair cuticle and into the polypeptide structure of the microfibril were investigated. Accordingly, an experiment was conducted on virgin hair that had not been previously conditioned or treated with any reducing agents. When this hair was exposed to a TCEP perming treatment a modest sulfur odor was observed. However, if this same hair was clipped with scissors into short lengths of approximately 1/8" to 1/4" long and then treated with TCEP there was a pronounced and noticeable odor of sulfur. The sulfur odor can be positively correlated with the degree and extent of disulfide bond cleavage.
  • An additional object of this invention is to avoid the use of strong reducing chemicals, requiring high pH for activity and provide instead, a medium in which the water-soluble phosphine reducing agent can engage in the necessary chemical reactions that lead to significantly improved hair perming, better hair styling and better overall hair care.
  • the present invention is directed to the use of a water-soluble tertiary phosphine as a reducing agent for altering the physical structure of hair.
  • the phosphine compound of Formula (I) can be used as the reactive agent needed to break disulfide bonds within an insoluble substrate, namely hair.
  • R ⁇ , R 2 and R 3 are preferably the same. More preferably, Ri, R 2 and R 3 are -(CH 2 ) 3 -OH, namely Tris-(3-hydroxypropyl)phosphine (THPP) or Ri, R 2 and R 3 are -(CH 2 ) 2 -COOH, namely Tris-(2- carboxyethyl)phosphine (TCEP).
  • THPP Tris-(3-hydroxypropyl)phosphine
  • TCEP Tris-(2- carboxyethyl)phosphine
  • Organic solvents are combined with these agents to lower the polarity of the composition thereby increasing the penetrating ability of the composition.
  • the composition may also advantageously contain a penetration enhancing agent.
  • THPP Tris-(3-hydroxyalkyl)phosphine
  • Tris-(3- hydroxypropyl)phosphine (THPP) also has superior hair perming ability and will help to circumvent some of the aforementioned problems.
  • THPP is a phosphine derivative that is water-soluble and lacks functional groups which can manifest a formal charge. This new molecule is shown below: CH 2 CH 2 CH 2 OH
  • THPP can penetrate into the interior polypeptide chains in the hair shaft because it lacks a formal charge and cannot form ionic bonds with positively charged functional groups. Also the treated hair can accept a stronger and longer lasting perm because THPP is a better nucleophile. The increased nucleophilicity is due to the electron releasing effects of the three hydroxypropyl chains attached to the phosphorus atom. As a consequence, the unshared pair of electrons on THPP phosphorus atom becomes more available for nucleophilic reactivity. More importantly, THPP can penetrate the hair effectively due to the absence of an acid chloride salt. In earlier perming reactions which utilized TCEP, it was necessary to neutralize the acid component of TCEP • HCI with base prior to use.
  • Suitable solvents include glycerine, low molecular weight glycol of CnH2n(OH)2 wherein n is 1-4, or polyethylene, polypropylene or polybutylene glycol of low, intermediate or high molecular weight, methyl end-cap glycol, monoglyme (ethylene glycol dimethyl ether), diglyme (2-methoxyethyl ether) and methylal (dimethoxymethane).
  • a relatively mild nonpolar solvent system such as 4% and 5% (v/v) methanol and 5% and 6% (v/v) ethanol.
  • EDTA ethylenediaminetetraacetic acid
  • I N 40g/l
  • 20N 800 ⁇ g/1 ⁇ l
  • This disclosure has focused on considering the role played by the polarity of the solvent system used to deliver the aforementioned phosphine reducing agents to the hair shaft polypeptide chains. Also considered was the need to remove the ionic charge from the phosphine reducing agent in order to deliver a more neutral molecule to the microfibril regions of the hair shaft. Moreover, the role of Na + CI " was evaluated as an additive to enhance THPP activity. However, when high salt concentration of sodium chloride were produced during the neutralization of TCEP, salt was found to inhibit the perming process.
  • viscosity and vapor pressure are intrinsic properties of any solvent system under consideration.
  • This alteration in solvent properties permits the active reagents greater access to the internal microfibril structure of the hair shaft thereby leading to a better perming of hair.
  • the vapor pressure of the solvent system plays an important role in helping to separate and open up the fine microfibril structure of hair.
  • An increased vapor pressure leading to enhanced solvent volatility with accompanying heat ranging in temperature from 45°C to 60°C facilitates the opening of interstitial spaces between the polypeptide chains and allows for the improved penetration of non-polar solvents along with reducing reagents.
  • THPP THPP
  • organic solvents such as methanol and ethanol are introduced to lower the solvent polarity.
  • THPP because of its lack of charge, is a more effective perming agent than TCEP.
  • THPP is better able to penetrate deeply into the hair shaft and it has a slightly increased nucleophilicity in comparison to TCEP. All of these properties contribute to the superior hair perming performance of THPP.
  • a second liposome, containing glucose oxidase is applied to the hair shaft which will react with the glucose previously deposited. There and only there, will hydrogen peroxide be generated in situ to set disulfide bonds into a permanent condition. This reaction leads to localized concentrations of hydrogen peroxide where glucose is deposited and avoids the traditional pitfalls using commonly applied oxidizing agents where hydrogen peroxide is used in excess and puts the consumer at risk.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne l'utilisation d'une phosphine tertiaire soluble dans l'eau en tant qu'agent réducteur pour modifier la structure physique du cheveu. Pour ce faire, les phosphines peuvent être utilisées en tant qu'agent réactif nécessaire pour rompre les liaisons bisulfure dans un substrat insoluble, à savoir le cheveu. C'est ainsi qu'on amorce la séquence de réduction permettant d'obtenir une ondulation ou un défrisage permanents du cheveu.
PCT/US1998/025169 1997-11-24 1998-11-24 Agent pour permanenter les cheveux ameliore Ceased WO1999026591A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16057/99A AU1605799A (en) 1997-11-24 1998-11-24 Improved hair perming agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US97748997A 1997-11-24 1997-11-24
US08/977,489 1997-11-24

Publications (2)

Publication Number Publication Date
WO1999026591A2 true WO1999026591A2 (fr) 1999-06-03
WO1999026591A3 WO1999026591A3 (fr) 1999-08-12

Family

ID=25525190

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/025169 Ceased WO1999026591A2 (fr) 1997-11-24 1998-11-24 Agent pour permanenter les cheveux ameliore

Country Status (2)

Country Link
AU (1) AU1605799A (fr)
WO (1) WO1999026591A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120031420A1 (en) * 2010-08-05 2012-02-09 John Gormley Composition and method for thermally activated hair treatment
US8192729B2 (en) * 2009-12-21 2012-06-05 Robert Saute Composition and method for hair straightening

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256154A (en) * 1963-10-18 1966-06-14 Gillette Co Hair waving composition and method
US3628910A (en) * 1966-05-02 1971-12-21 American Cyanamid Co Compositions for the deformation of keratin
FR1574239A (fr) * 1967-07-12 1969-07-11
US5690956A (en) * 1995-09-27 1997-11-25 Sdg, Inc. Hair care perming agent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8192729B2 (en) * 2009-12-21 2012-06-05 Robert Saute Composition and method for hair straightening
US20120031420A1 (en) * 2010-08-05 2012-02-09 John Gormley Composition and method for thermally activated hair treatment
US8673276B2 (en) * 2010-08-05 2014-03-18 Grant Industries, Inc. Composition and method for thermally activated hair treatment

Also Published As

Publication number Publication date
AU1605799A (en) 1999-06-15
WO1999026591A3 (fr) 1999-08-12

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